Will Shortz surrounded by his collection of
crossword puzzles at his home in
Pleasantville, New York

Will. Shortz ’77. Writes. One. Word. At. A. Time.

Cullen Couch

QUITE LITERALLY, LAWYERS are only as good as their words, so it should come as no surprise that a Law School graduate is the world’s foremost authority on the venerable crossword puzzle first introduced in this country in 1913.

Will Shortz ’77, the New York Times crossword puzzle editor since 1993 and Puzzle Master of National Public Radio’s Weekend Edition since the program first aired in 1987, has been transfixed by puzzles since he was young boy when his mother gave Shortz a piece of paper ruled into squares. She showed him how to interlock words within the squares and he was happy doing so all afternoon. In fact, he’s been happy about it ever since, pursuing a passion that has taken him to the highest perch in the puzzling world.

He sold his first crossword puzzle when he was 14 and went to college determined to parlay his passion into a bachelor’s degree. He proposed to the administration at Indiana University a degree and sketched out course requirements for a historical and analytical study of puzzling. They accepted his proposal; he now holds the world’s first and only degree in enigmatology (as far as Shortz can tell). Following the lead of his older brother who had become a lawyer, he earned his J.D. at the Law School and ultimately used his legal training to develop the business savvy for pursuing a freelance career (not to mention hone his puzzling skills).

“The greatest benefit of Law School to me,” he says, “was to learn how to take apart a complex issue and deal with each part separately until you’ve solved it. That’s good training for puzzles and it’s good training for life. I also learned how the world works and how business works. I’m essentially a freelance person so that helped me in many ways. Since my undergraduate degree was in enigmatology, which no one really takes seriously, my law degree from the University of Virginia gave me a substance that I wouldn’t have had otherwise.”

Yet his fans think Shortz has a great deal of substance. More than 40,000 Times readers subscribe to his paper’s online crossword subscription service; he has written or edited more than 100 puzzle books that a worldwide market gobbles up; and he charms his weekly audience at NPR with his clever puzzles and affable repartee with host Lianne Hansen. He founded the annual American Crossword Puzzle Tournament in 1978 and the World Puzzle Championship in 1992, and has collected more than 20,000 puzzle books and magazines from all over the world, which he houses at his beautiful Tudor home in Pleasantville, NY. Shortz’s celebrity status and financial success are remarkable in a field not known for either.

“I always wanted a career in puzzles,” says Shortz in recalling his decision to go to the Law School. “I just didn’t think it would be financially feasible. It’s hard to make a living constructing puzzles. So my idea was to practice law for ten years and make enough money so that I could then shift into what I really wanted to do.”

He started Law School in the fall of 1974. “It was fine,” he recalls, but by the spring of his first year, Shortz had decided that he wasn’t going to practice law. He therefore took the courses that interested him without worrying about their ultimate usefulness to a legal career. “I could get pretty good grades, and take only what I wanted to take, like a fascinating course on socialist legal systems and several courses on intellectual property and copyrights and patents. I also wrote a paper on copyright protection for puzzles and games, which helped my puzzling career.” He eventually landed the most prestigious position in the crossword world.

“When I was a kid, I never dreamed that I would be the Times crossword editor. It felt like an intellectual, literary sort of job that was beyond me. But I love to read and I love to learn, so that’s never been a problem. The nice thing about the Times job is that I can do anything I want with it. No one’s asking me to change this clue or do something else. It appears in the newspaper. They know it’s popular and just leave me alone, which is great.”

Shortz recalls the difficulties of his first year at the Times. His predecessors, Will Weng and Eugene Maleska, had died, so he had no one to go to for advice. He began constructing puzzles based on what he knew as a former Games magazine editor. The regular Times solvers objected, saying the puzzles were for younger people and were too easy. “They wanted hard puzzles,” says Shortz, “so I thought, by God, if these solvers want hard puzzles I’ll show them how hard it is. I started making everything really hard, then got letters the other way. I then settled into a pattern where the difficulty would increase through the week.”

Shortz increases the difficulty of his puzzles in a number of ways. Most important is the puzzle’s inherent difficulty; a crossword using obscure words is going to be harder. He also uses the crossword theme: it’s easier if it uses phrases that everyone knows and harder if it involves puns, trickery, dropping letters, or other deceptive techniques. A crossword that has just a few black squares and lots of white squares is harder because the words are longer. For a Monday puzzle, he makes the clues as easy as he can, consistent with having them fresh. On Friday and Saturday, he makes them as hard as he can, consistent with being fair.

Shortz also creates two puzzles every week for NPR’s Weekend Edition. He often gets his ideas lying in bed at night trying to think of some constraint that will create a new solving situation. For example, “Try this,” he says with a wry grin. “The made-up word VALUE-WARY can be transposed into a familiar two-word phrase naming someone who is generally held in high respect. Who is it?”